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Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
The price is €141
includes taxes & fees
18 Nov - 19 Nov
First Floor Studio Apartment in Historic Chestertown

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Arnold
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
United States
Nathan M.
The price is €352
includes taxes & fees
18 Nov - 19 Nov
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Guest Suite for up to 2 in a Victorian on the Chester River

Millington
9.6 out of 10, Exceptional, (19)
"It was very clean and cozy! My partner and I loved staying here! "
United States
Tyaunna W.
The price is €112
includes taxes & fees
18 Nov - 19 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
10.0 out of 10, Exceptional, (1)
The price is €396
includes taxes & fees
18 Nov - 19 Nov
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Great little getaway, very clean, and the bedding was so comfy! "
United States
Joan F.
The price is €257
includes taxes & fees
2 Dec - 3 Dec
Small House on Gentleman’s Farm

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (42)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is €214
includes taxes & fees
18 Nov - 19 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is €224
includes taxes & fees
19 Nov - 20 Nov
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

2.0 star property
Berea
9.6 out of 10, Exceptional, (4)
"Crystal was a wonderful host with great communication! The check in process was simple and the house was tidy; would definitely recommend. "
United States
Mekiyah H.
The price is €181
includes taxes & fees
18 Nov - 19 Nov
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

Hudson house

3.5 star property
Canton
The price is €290
includes taxes & fees
18 Nov - 19 Nov
Hudson house

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is €251
includes taxes & fees
18 Nov - 19 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Hobbit House one of a kind home

Bel Air
10.0 out of 10, Exceptional, (7)
"We had a great stay! "
United States
Courtney H.
The price is €262
includes taxes & fees
18 Nov - 19 Nov
Hobbit House one of a kind home

Exclusive Sunken Living Room Soaring Exposed Brick

Patterson Place
10.0 out of 10, Exceptional, (6)
"Our stay was absolutely wonderful! The amenities that Matthew provided were great -- there were mints, lollypops, and granola bars for each of us upon arrival. The space is incredible! From the Master Suite with a king-sized bed that was adjustable to the other bedrooms that were comfortable and cozy. Also, we loved the small details, like the beautiful paintings and decorations, plus the "Baltimore Bucket List" to check-off. Everything was clean and neat, and anytime we had a question, Matthew...
United States
Julie B.
The price is €285
includes taxes & fees
18 Nov - 19 Nov
Exclusive Sunken Living Room Soaring Exposed Brick

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (33)
"This was a great place to stay with everything you needed. I loved the furniture in the house and it was well decorated, not to mention the neighborhood was quiet and close to all these good restaurants. Parking was a breeze for us since we drove in two cars. We parked in the wrap around driveway. There is a small fenced in back yard so it was perfect to let the dog run around and do his business. The host was great and couldn’t have asked for a better stay. "
United States
Mateusz K.
The price is €270
includes taxes & fees
20 Nov - 21 Nov
Large 2 bedroom house with private parking in a nice neighborhood

Johns Hopkins Historic Renovated home - Location!

Upper Fells Point
9.4 out of 10, Exceptional, (13)
"Beautiful home! We stayed for one night- everything was clean, easy check in, easy to find street parking and we felt safe and comfortable staying here. "
United States
Rhianna G.
Johns Hopkins Historic Renovated home - Location!

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €391
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is €369
includes taxes & fees
18 Nov - 19 Nov
Grandma’s Cottage will wrap around you like a warm hug

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is €393
includes taxes & fees
18 Nov - 19 Nov
HGTV quality, private guest suite, country getaway with hot tub & fire pit

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
8.4 out of 10, Very good, (7)
"We were in town for a family wedding and needed a peaceful "home base" to relax and get ready. "The Hideaway Spot" was absolutely perfect! It is an upscale nautical cabin-like interior with plenty of room for 2 couples. The outside deck was great for coffee and chilling together. Peaceful getaway from hustle and bustle of the city. Plenty of fabulous seafood in Glen Burnie nearby. Communication with host was easy with prompt responses and attention to any requests/questions we had. The family...
United States
Ashlee H.
The price is €307
includes taxes & fees
18 Nov - 19 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Modern New Suite Close to US Capital and BWI Airport

Pasadena
7.0 out of 10, Good, (2)
"Great location but horrible noise level AT the property as well as someone else’s hair in the carpets in our room. The property manager communicated well, however, we shouldn’t have had to ask on more than one occasion for his tenant to stop playing his game so loudly at night. We also shouldn’t have had someone else hair in our room and on our belongings. Would not stay again. "
United States
Lenny J.
The price is €131
includes taxes & fees
6 Dec - 7 Dec
Modern New Suite Close to US Capital and BWI Airport

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"Loved sitting on the dock, peaceful, quiet; house has everything you need"
United States
jackie r.
The price is €278
includes taxes & fees
18 Nov - 19 Nov
Waterfront Retreat with Private Dock and Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Chestertown is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table.

How many holiday rentals are there in Chestertown?

Expedia has 24 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.